Are you too senior to go 1099?

In my book, I make a point that if you're already pretty senior (management level) at a company, it will be a little tricky to go 1099 (at least, using my methods) as there are less spots for senior people and most companies won't want to bring on a management level person as a 1099.

I think if you're at this level, you have a few options.

The first option is to fall back to an individual contributor type role. This might mean going back to doing work you did a few years ago, if you still have those skills. You would probably be a Subject Matter Expert (SME) and lean heavily on your client relationships to pull this off.

The second option is to go straight to building a company. Presumably if you're senior enough, you have the experience and the network to convince four or five people to come work for you, and then find a friendly prime to bring on your company to an existing contract or a future proposal. You can take one of the positions for yourself so you're billable.

It will come down to a personality/interest thing. If you like being a SME and not managing people, pick option one. If you like the idea of being a business owner and growing a successful company, pick option two.

Either way, I don't think it's impossible to become a 1099 if you're very senior, I think it's just less straightforward because there are fewer opportunities at a higher level.

Want the full playbook? Check out Going 1099.